Reaktion #10492

Reaktionsgleichung

Et3N

ethyl ester

Methanesulfonic acid 2-(5-bromo-benzothiazol-2-yl)-ethyl ester

2-(R)-methyl pyrrolidine

→

5-Bromo-2-[2-(2-(R)-methyl-pyrrolidin-1-yl)-ethyl]-benzothiazole

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was removed under vacuum
2. 2
   workup.DISSOLUTIONthe residue dissolved in CH2Cl2
3. 3
   Waschenwashed with saturated NaHCO3 (twice)
4. 4
   TrocknenThe organic layer as dried over MgSO4
5. 5
   Einengenconcentrated in vacuo
6. 6
   Sonstigeto give crude product, 1.15 g (97.1%)

Vorschrift

The methanesulfonic acid 2-(5-bromo-benzothiazol)-2-yl)-ethyl ester from Example 1B, and 2 equivalents (7.3 mmol) of 2-(R)-methyl pyrrolidine (at a concentration of 10 mg/mL solution in acetonitrile), was combined with excess Et3N (0.99 g, 9.8 mmol), and the resulting mixture was heated to 60° C. for 2 hr. The solvent was removed under vacuum, and the residue dissolved in CH2Cl2, and washed with saturated NaHCO3 (twice). The organic layer as dried over MgSO4 and concentrated in vacuo to give crude product, 1.15 g (97.1%). 1H NMR (400 MHz, CDCl3) δ ppm 1.06 (d, J=6.04 Hz, 3 H) 1.78–1.6 (m, 3 H) 1.88 (m, 1H) 2.20 (m, 1 H) 2.38 (m, 1H) 2.55 (m, 1H) 3.23 (m, 4 H) 7.37 (dd, J=8.44, 1.85 Hz, 1 H) 7.61 (d, J=8.51 Hz, 1 H) 8.02 (d, J=1.92 Hz, 1 H). MS m/z 125, 127 (M+H)+, (M+3H)+.

Quelle